EP4029872B1 - Composé de métal de transition, son procédé de préparation et composition de catalyseur le comprenant - Google Patents

Composé de métal de transition, son procédé de préparation et composition de catalyseur le comprenant Download PDF

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EP4029872B1
EP4029872B1 EP21852855.2A EP21852855A EP4029872B1 EP 4029872 B1 EP4029872 B1 EP 4029872B1 EP 21852855 A EP21852855 A EP 21852855A EP 4029872 B1 EP4029872 B1 EP 4029872B1
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room temperature
chemical formula
transition metal
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EP4029872A4 (fr
EP4029872A1 (fr
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Byung Seok Kim
Minyoung Kang
Insun LEE
Seok Hwan Kim
Donghyeon GWON
Yoonchul JUNG
Seyoung Kim
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LG Chem Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F17/00—Metallocenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/1616—Coordination complexes, e.g. organometallic complexes, immobilised on an inorganic support, e.g. ship-in-a-bottle type catalysts
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F210/02—Ethene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F210/14—Monomers containing five or more carbon atoms
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    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F210/16—Copolymers of ethene with alpha-alkenes, e.g. EP rubbers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00—Polymerisation catalysts
    • C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
    • C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
    • C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
    • C08F4/62—Refractory metals or compounds thereof
    • C08F4/64—Titanium, zirconium, hafnium or compounds thereof
    • C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00—Polymerisation catalysts
    • C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
    • C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
    • C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
    • C08F4/62—Refractory metals or compounds thereof
    • C08F4/64—Titanium, zirconium, hafnium or compounds thereof
    • C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
    • C08F4/65908—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an ionising compound other than alumoxane, e.g. (C6F5)4B-X+
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00—Polymerisation catalysts
    • C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
    • C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
    • C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
    • C08F4/62—Refractory metals or compounds thereof
    • C08F4/64—Titanium, zirconium, hafnium or compounds thereof
    • C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
    • C08F4/65912—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an organoaluminium compound
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00—Polymerisation catalysts
    • C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
    • C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
    • C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
    • C08F4/62—Refractory metals or compounds thereof
    • C08F4/64—Titanium, zirconium, hafnium or compounds thereof
    • C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
    • C08F4/6592—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00—Polymerisation catalysts
    • C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
    • C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
    • C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
    • C08F4/62—Refractory metals or compounds thereof
    • C08F4/64—Titanium, zirconium, hafnium or compounds thereof
    • C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
    • C08F4/6592—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
    • C08F4/65922—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not
    • C08F4/65927—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not two cyclopentadienyl rings being mutually bridged
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2410/00—Features related to the catalyst preparation, the catalyst use or to the deactivation of the catalyst
    • C08F2410/02—Anti-static agent incorporated into the catalyst
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2420/00—Metallocene catalysts
    • C08F2420/07—Heteroatom-substituted Cp, i.e. Cp or analog where at least one of the substituent of the Cp or analog ring is or contains a heteroatom
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2420/00—Metallocene catalysts
    • C08F2420/10—Heteroatom-substituted bridge, i.e. Cp or analog where the bridge linking the two Cps or analogs is substituted by at least one group that contains a heteroatom
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00—Polymerisation catalysts
    • C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
    • C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
    • C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
    • C08F4/62—Refractory metals or compounds thereof
    • C08F4/64—Titanium, zirconium, hafnium or compounds thereof
    • C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
    • C08F4/65916—Component covered by group C08F4/64 containing a transition metal-carbon bond supported on a carrier, e.g. silica, MgCl2, polymer

Definitions

  • a polyolefin polymer having a broad molecular weight distribution while containing a large amount of comonomer in the polyolefin at high molecular weight side that is, a polyolefin with a reinforced BOCD (Broad Orthogonal Comonomer Distribution) structure.
  • the polyolefin having such a structure can be suitably used as a product for injection, because its mid-to-long-term durability is strengthened. Accordingly, efforts to develop a metallocene catalyst capable of providing a polyolefin having a BOCD structure are continuing, and in particular, the high molecular weight and high comonomer incorporation metallocene catalysts are not diverse, and the development thereof is required.
  • the hybrid supported catalyst according to an embodiment of the present disclosure may further include a cocatalyst in addition to the transition metal compound represented by Chemical Formula 1 and the support.
  • the cocatalyst may include at least one of compounds represented by the following Chemical Formula 3 or Chemical Formula 4. [Chemical Formula 3] -[Al(R 31 )-O] m - in Chemical Formula 3,
  • the olefinic monomer may include ethylene, propylene, 1-butene, 1-pentene, 4-methyl-1-pentene, 1-hexene, 1-heptene, 1-octene, 1-decene, 1-undecene, 1-dodecene, 1-tetradecene, 1-hexadecene, 1-eicosene, norbornene, norbornadiene, ethylidenenorbornene, phenylnorbornene, vinylnorbornene, dicyclopentadiene, 1,4-butadiene, 1,5-pentadiene, 1,6-hexadiene, styrene, alpha-methylstyrene, divinylbenzene, and 3-chloromethylstyrene, and may be copolymerized by mixing two or more of these monomers.
  • the ligand was dissolved in a mixed solvent of toluene:ether (2:1, 0.53 M), and n-BuLi (2.05 eq) was added at -25 °C, followed by stirring at room temperature for 5 hours.
  • a slurry was prepared by mixing ZrCl 4 (1 eq) with toluene (0.17 M) in a flask, and added thereto, followed by stirring overnight at room temperature.
  • 2-iPr-4-tBuPhlndene (1 eq) was dissolved in a mixed solvent of toluene:THF (10:1, 0.5 M), and n-BuLi (1.05 eq) was slowly added dropwise thereto at -25 °C, followed by stirring at room temperature for 3 hours. Thereafter, dichloro methyl phenyl silane (1.05 eq) was added thereto at -10 °C, and stirred overnight at room temperature.
  • the ligand was dissolved in a mixed solvent of toluene:ether (2:1, 0.53 M), and n-BuLi (2.05 eq) was added at -25 °C, followed by stirring at room temperature for 5 hours.
  • a slurry was prepared by mixing ZrCl 4 (1 eq) with toluene (0.17 M) in a flask, and added thereto, followed by stirring overnight at room temperature.
  • the weight average molecular weight (Mw) was measured using gel permeation chromatography (GPC).

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Claims (13)

  1. Composé de métal de transition représenté par la formule chimique 1 suivante :
    Figure imgb0050
     dans la formule chimique 1,
    M est un métal de transition du groupe 4 :
    X1 et X2 sont chacun indépendamment un hydrogène ; un halogène ; ou un alkyle en C1-20 ;
    A est du carbone ou du silicium,
    R11 et R12 sont chacun indépendamment un hydrogène ; un halogène ; un alkyle en C1-20 ; un alcoxyalkyle en C2-20 ; ou un aryle en C6-20 ;
    R21 est du méthyle,
    R22 est un alkyle en C3-20 ; un alcoxyalkyle en C3-20 ; ou un alcényle en C3-20,
    R23 est un aryle en C6-20 non substitué ; ou un alkylaryle en C7-20,
    R24 et R25 sont chacun un hydrogène ; ou R24 et R25 sont reliés l'un à l'autre pour former un cycle cycloalcane en C3-10,
    R26 est un alkyle en C1-20, et
    R27 est un aryle en C6-20 non substitué ; ou un alkylaryle en C7-20.
  2. Composé de métal de transition selon la revendication 1,
    dans lequel M est du zirconium ou du hafnium, et
    X1 et X2 sont chacun indépendamment un halogène.
  3. Composé de métal de transition selon la revendication 1,
    dans lequel A est du silicium, et
    R11 et R12 sont chacun indépendamment un alkyle en C1-10 ; un alcoxyalkyle en C2-10 ; ou un aryle en C6-10.
  4. Composé de métal de transition selon la revendication 1,
    dans lequel R22 est un alkyle en C3-10 ; un alcoxyalkyle en C3-10 ; ou un alcényle en C3-10.
  5. Composé de métal de transition selon la revendication 1,
    dans lequel R23 est un phényle non substitué ; ou un phényle substitué par un alkyle en C1-10.
  6. Composé de métal de transition selon la revendication 1,
    dans lequel R24 et R25 sont chacun un hydrogène ; ou R24 et R25 sont reliés l'un à l'autre pour former un cycle cyclopentane, ou un cycle cyclohexane.
  7. Composé de métal de transition selon la revendication 1,
    dans lequel R27 est un phényle non substitué ; ou un phényle substitué par un alkyle en C1-10.
  8. Composé de métal de transition selon la revendication 1,
    dans lequel M est du zirconium ou du hafnium,
    X1 et X2 sont chacun indépendamment un halogène,
    A est du silicium,
    R11 et R12 sont chacun indépendamment un alkyle en C1-10 ; un alcoxyalkyle en C2-10 ; ou un aryle en C6-10,
    R22 est un alkyle en C3-10 ; un alcoxyalkyle en C3-10 ; ou un alcényle en C3-10,
    R23 est un phényle non substitué ; ou un phényle substitué par un alkyle en C1-10,
    R24 et R25 sont chacun un hydrogène ; ou R24 et R25 sont reliés l'un à l'autre pour former un cycle cyclopentane, ou un cycle cyclohexane, et
    R27 est un phényle non substitué ; ou un phényle substitué par un alkyle en C1-10.
  9. Composé de métal de transition selon la revendication 1,
    dans lequel le composé de métal de transition représenté par la formule chimique 1 est un quelconque sélectionné dans le groupe constitué de :
    Figure imgb0051
    Figure imgb0052
    Figure imgb0053
    Figure imgb0054
    Figure imgb0055
  10. Procédé destiné à préparer un composé de métal de transition selon la revendication 1, comprenant les étapes de :
    préparer un composé représenté par la formule chimique 1-1 suivante en faisant réagir un composé représenté par la formule chimique a suivante avec un composé représenté par la formule chimique b suivante ;
    préparer un composé représenté par la formule chimique 1-2 suivante en faisant réagir un composé représenté par la formule chimique 1-1 suivante avec un composé représenté par la formule chimique 1-11 suivante ; et
    préparer un composé représenté par la formule chimique 1 suivante en faisant réagir un composé représenté par la formule chimique 1-2 suivante avec un composé représenté par la formule chimique 1-21 suivante :
    Figure imgb0056
    Figure imgb0057
     où
    M, X1, X2, A, R11, R12, et R21 to R27 sont tels que définis dans la formule chimique 1, et
    chaque X' est indépendamment un halogène.
  11. Composition de catalyseur comprenant le composé de métal de transition selon la revendication 1.
  12. Composition de catalyseur selon la revendication 11,
    comprenant en outre au moins un cocatalyseur sélectionné dans le groupe constitué de composés représentés par les formules chimiques 3 et 4 suivantes :

            [Formule chimique 3]     -[Al(R31)-O]m-

    dans la formule chimique 3,
    chaque R31 est indépendamment un halogène, un alkyle en C1-20 ou un haloalkyle en C1-20 ; et m est un nombre entier de 2 ou plus ;

            [Formule chimique 4]     J(R32)3

    dans la formule chimique 4,
    chaque R32 est indépendamment un halogène, un alkyle en C1-20 ou un haloalkyle en C1-20 ; et
    J est de l'aluminium ou du bore.
  13. Procédé destiné à préparer une polyoléfine, comprenant une étape de polymérisation de monomères oléfiniques en présence de la composition de catalyseur selon la revendication 11.
EP21852855.2A 2020-08-04 2021-07-06 Composé de métal de transition, son procédé de préparation et composition de catalyseur le comprenant Active EP4029872B1 (fr)

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PCT/KR2021/008586 WO2022030769A1 (fr) 2020-08-04 2021-07-06 Composé de métal de transition, son procédé de préparation et composition de catalyseur le comprenant

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TW294669B (fr) * 1992-06-27 1997-01-01 Hoechst Ag
US20050182266A1 (en) * 2002-06-12 2005-08-18 Schulte Jorg L. Transition metal componds their preparation and their use in catalyst systems for the polymerization and copolymerization of olefins
CN106459278B (zh) * 2014-04-17 2020-11-06 博里利斯股份公司 用于以高温溶液聚合法制备聚乙烯共聚物的经改善的催化剂体系
KR101711788B1 (ko) * 2016-03-09 2017-03-14 한화케미칼 주식회사 혼성 촉매 조성물, 이의 제조방법, 및 이를 이용하여 제조된 폴리올레핀
KR20180054357A (ko) * 2016-11-15 2018-05-24 주식회사 엘지화학 폴리프로필렌의 제조방법

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EP4029872A4 (fr) 2023-02-01
CN114599661B (zh) 2024-03-12
KR20220017199A (ko) 2022-02-11
WO2022030769A1 (fr) 2022-02-10
CN114599661A (zh) 2022-06-07
EP4029872A1 (fr) 2022-07-20

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